


Sweet Transvestite

by GabrielsCupcake



Category: Rocky Horror Picture Show, Supernatural
Genre: F/M
Language: English
Status: In-Progress
Published: 2015-06-10
Updated: 2015-07-24
Packaged: 2018-04-03 18:22:33
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 4,584
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4110604
Author URL: https://archiveofourown.org/users/GabrielsCupcake/pseuds/GabrielsCupcake
Summary: <blockquote class="userstuff">
              <p>Your father (Bobby) died and you break down in front of a house.</p>
            </blockquote>





	1. Sweet Transvestite

**Author's Note:**

> So this isn't confusing I'll give you the gist of the plotline if you don't want Spoilers don't read this...
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> SPOILERS!!!! Your boyfriend is Lucifer and after your father dies Lucifer tries to make you feel better by playing out one of your biggest fantasies (which he only knows about because he read your diary), Musical role play. He'll be doing other musicals later but right now it's The Rocky Horror Picture Show.

Lucifer Rocky Horror Picture Show, plays out a fantasy you’ve had to make you feel better after your father Bobby’s death

“Balls!!!” you yelled slamming your hand down on the steering wheel. Your car had just broke down in the middle of fucking nowhere, and you had nothing to repair the car with or call anyone to come get you. The only sign of life in this barren wasteland was a creepy old abandoned house (little did you know it was anything but… abandoned that is).

You sighed and got out of the car, stepping into the pouring rain and kicked the wheel angrily. You opened the boot of your car and picked a couple weapons, 2 _Salt-Guns, Holy Water and an Angel Blade, yep good enough._ You were the daughter of the famous Bobby Singer, you knew better than to walk in anywhere empty handed. You may not have been in your right mind at the moment, because of your dads death but buggered if you were insane enough to walk around without a couple of weapons, especially not when entering a creepy house.

You closed the boot and made your way to the front door, knocking twice with your gun before entering. You screamed when you were suddenly attacked by an unknown, and unexpected monster. The giant thing had grabbed you from behind and no matter what you did you could not escape his monstrously tight grip. You looked up when a man’s voice shouted “Gabriel let her go.”

He was a strange looking man, with blonde hair, blue eyes and a strangely rotting face and he was dressed in drag. He was wearing black eye liner, mascara and eye shadow and dark red lipstick, black leather pants and black stilettos, and with each step he took down the tall staircase a light flickered on above him.

He smiled and opened his mouth to say something else and instead started singing. “How d'you do, I see you've met my faithful handyman. He’s just a little brought down because when you knocked, he thought you were the candy man” as he sang instrumental accompaniment appeared out of nowhere and began to play along with him. He reached the floor before singing the next line, “don’t get strung out, by the way I look” he sang running his hands down his body “don’t judge a book by its cover.” He was now making his way toward you, “I’m not much of a man, by the light of day but by night I’m one hell of a lover” he sang running his hand down your arm. Instead of putting up a fight the way you should you just shivered and let out a small groan, this made the man smile wider as he continued to sing.

“I’m just a sweet transvestite”

“Sweet transvestite” sang the harmonious voices of three woman, who like the instrumentalists appeared out of nowhere.

“From transsexual, Transylvania.” He thrust his hips at that and you gulped. “Let me show you around, or play you a sound, you look like your pretty groovy. Or if you want something visual, that’s not to abysmal we can take in an old Steve Reeves movie”

You go to speak but end up singing your words instead, “Glad I caught you at home, can I use your phone? I’m in a bit of a hurry, I’ll just say were we are, than go back to the car, I don’t want to be any worry.”

“Well you got caught with a flat, well, how ‘bout that, baby don’t you, worry. By the light of the night when it all seems alright, I’ll get you a satanic mechanic” he smirked at this and pushed you back into a seat that just appeared behind you and straddled your lap.

“I’m just a sweet transvestite”

“Sweet transvestite” the back-up singers sang again.

“From Transsexual, Transylvania.” He sang running his hands up your arms towards your shoulders which were resting on the arms of the chair. “Why don’t you stay for the night”

“Night” you heard someone whisper.

“Or maybe a bite” he said biting at you. You swallowed and unconsciously bucked your hips, this man was, strangely enough, quite sexy.

“Bite” someone else whispered.

“I could show you my favourite obsession.” He gets off you, and you whimper at the loss of his weight on your lap, you could feel yourself already starting to grow wet for the strange man, it was kind of embarrassing how worked up he was getting you.

He starts walking away from you as he sings the next line, “I’ve been making a man, with blonde hair and a tan, and he’s good for relieving my,” he turns the top half of his body to face you as he sings the next bit “tension.”

He turns around and continues singing as he walks back to you “I’m just a sweet transvestite”

“Sweet transvestite” the backing vocalists sang again.

“From Transsexual Transylvania.” He repeats what was obviously the chorus again “I’m just a sweet transvestite”

“Sweet transvestite”

“From Transsexual Transylvania.” He pauses for a bit and you start to think he may be finished so you go to clap but he stops you in your tracks and starts singing again.

“So come up to the lab. And see what’s on the slab. I see you shiver with, antici” he pauses “pation. But maybe the rain, isn’t really to blame. So I’ll remove the cause,” he chuckles darkly “but not, the symptoms!” As soon as the song ended the lights flicked off and when they turned back on you were in an empty room and all evidence that had happened was gone.


	2. Touch Me

**Summary for the Chapter:**

> You see how much of a lover your sweet transvestite can be.

**Notes for the Chapter:**

> This chapter was meant to be a songfic like all the other chapters but I started writing this story before I downloaded the song, so you'll just have to listen to the song when you read this chapter. If I get enough requests to rewrite this chapter as a songfic though, I may post a songfic version. Oh and this chapter contains smut so if you don't like that kind of stuff, wait for the next chapter, but there will be a lot of smut in this story. Oh and this was my first smut fanfiction, so it may not be very good, I hope you enjoy.

You compose yourself and start looking around the place, curious as to what other strange wonders you’d come across. You were still cautious but nothing bad had happened and you were intrigued, plus you really wanted to see what was on the slab. You chuckled quietly to yourself as you thought of what he might’ve meant by that and continued to search. Finally you came across a room with black painted walls and nothing but a canopy bed in the centre of the room.

You yawned and entered closing the door behind you, you were quite tired, maybe you could continue your search later. You walked across the room and climbed into the bed curling up with the blankets and closing your eyes. You let out a scream when you felt an arm wrap around you. “What the hell?” You mumbled opening your eyes and sitting up to try and see your attacker in the darkness.

“Hush honey, it’s only me” said the voice that sounded like the sweet transvestite. Suddenly the room was illuminated by several candles and you were pushed back onto the soft bed by the blonde haired man. He slowly kissed down your chest as he unbuttoned the white blouse you were wearing. You were wearing a tight, white blouse, a lacy black bra and navy denim jeans with knee-high army boots.

You groaned but gained a moment of clarity, “this is wrong I barely know you.”

He smirked and pulled off your now unbuttoned blouse as he planted a kiss on your stomach, “it’s a great way to get to know you, and I’ll find out what you like and don’t like.” He purred slowly unbuttoning your pants and pulling them off, your boots having already disappeared, “plus I see you’ve come prepared.” He says pushing a finger inside you “and oh, already so wet for me.”

You whimpered and bucked your hips “I always come prepared.”

He dragged himself up your body leaving a trail of kisses as he went and you reached down to undo his pants as you let lust overcome you. It had been a couple of months since the last time you made love to someone, and for a hunter that was the equivalent of several decades. Besides you needed the relief and this man was offering, so why the hell not? You pulled down his pants and chuckled when his large member sprang out at you. “I see I’m not the only one who comes prepared.”

“No, but tonight you’re the one who cums first.” He growls back biting at your neck.

You groaned and let your hand tangle in his hair as the other reached down to grab his member. “Uh-uh-uh” he tuts at you, slapping your hand away. “Not yet, I wouldn’t be one hell of a lover if I let you have me so quickly, you need to be patient my dear. Or I’ll have to chain you up.”

You swallowed and pulled your arms back resting them above your head. “That’s a good girl” he purrs travelling down your body to your dripping pussy. He flicks your clit with his forked tongue before dipping it inside of you, earning a scream of pleasure from you. He smirked at this and dove his tongue further inside you, you bucked your hips and he hissed the sound making his tongue flick inside you and you grabbed his hair “f-fuck.”

He growled and looked up at you as he moved to suck on your clit again, you could feel yourself on the verge of orgasm, you were already close from earlier and his actions now were just stoking the fire inside you. “Please” you begged tugging on his hair to try and pull him up.

“Well since you asked so nicely” he chuckles, crawling up your body so his strong, masculine figure rubbed against yours. You shivered and grabbed his head to kiss him and he slid into you, making you whimper.

You gasped and dragged your nails down his back earning a snarl from him, he pulled away from the kiss and bit your neck. You screamed in pleasure and wrapped your legs around him digging your heels into his ass as he thrust faster and faster into you. You were so close and it was starting to hurt trying to stave off your orgasm. But you wanted him to cum with you.

“Please Luci, I’m so close, I want you to cum with me,” you whine. He kisses you gently and nods “ok sweetheart, just hold on. If that’s what you want I’ll give it to you, but I’m not there just yet, hang on baby,” he whispers. He was getting closer, but he wasn’t quite there a couple more thrusts though and he was finally spilling into you, howling with pleasure, this was all you needed and you came with him clamping hard around him.

When you both caught your breath he pulled out of you and rolled the two of you over so he was laying back on the bed and you were resting gently in his arms. He kissed your cheek and chuckled, “you broke character.”

“And you cheated” you retorted.

“How did I cheat?” Lucifer asked.

“The real Dr Frank-n-Furter is an alien, not an angel. He can’t just snap his fingers and make things appear and disappear from thin air.” You said stroking your partners chest.

“That’s true, and I’m glad if you had to call out a name that you did break character. I’d rather you say my name, than someone else’s, even if we are role-playing.” He smiles stroking your hair.

You sighed and asked “speaking of role-play, how did you know this was a fantasy of mine?”

Lucifer smirks “I may have accidentally read your diary. At first I thought it was just fan fiction ideas, I mean I know how much you like to write. But then I finally came across a page with the words ‘it’d be really awkward if anyone ever read this.’ Instantly I shut the book but by then I had already read about your musical kink, and when I heard about…” he stops himself before he can say anything that might upset you, “I thought this would be a good way of cheering you up, I’m sorry if I…”

You stopped him mid-sentence and smiled, “thank you Luci, that’s the nicest thing anyone’s ever done for me, and I mean you even got Gabriel to help you, admittedly he’d probably jump at something like this especially if it meant he got to see his big brother dressed in drag but still… I don’t care that you read my diary, your my partner I shouldn’t be keeping secrets from you anyway, from now on I’m gonna share everything with you. Well I mean everything you need to know, if it gets me moments like this I’ll tell you anything.”

He chuckled “shh babe your rambling,” he said kissing your cheek. You blushed and apologised, “it’s ok. You know maybe next time we can do Mamma Mia.”

You looked at him excitedly “does that mean we’re going to Greece?”

“If you want.” He promised smirking at the fact that you didn’t get the hint.

You beamed happily and curled up in his arms, “thank you” you mumbled closing your eyes and slowly drifted off to sleep.

“Your welcome,” he said, you didn’t hear him though because you were now fast asleep.

**Notes for the Chapter:**

> Thanks for reading, I hope you enjoyed. I'm sorry if the smut was shit...


	3. The Winner Takes It All

**Summary for the Chapter:**

> Tickets to greece and a wedding invitation? That can only mean one thing... It's time for a Mamma Mia song chapter.

**Notes for the Chapter:**

> This probably won't be too good. But I hope you enjoy.

“What the?” You mumble as you wake up the next morning to an empty bed, you sit up and look around the room and spot an envelope. You open it and find a wedding invitation, a plane ticket to Greece and a note with three simple words, “Remember, play along.”   
You received the exact same note right before the events of your Sweet Transvestite role play, and if that was anything to go by this would be good. When you got the first note though, you were driving to nowhere in particular, the co-ordinates had popped up on your GPS and the sticky note on your steering wheel. It had scared the hell out of you and you were almost involved in a car accident, but luckily you gained enough focus to calm down and pull over to the side of the road. You were confused by the note but also intrigued, and so you followed the co-ordinates, making sure to bring protection just in case it was a trap. But when you saw the familiar face of your lover you remembered the words, “remember, play along,” and so you did, and let’s just say you were not disappointed.  
So this time round knowing what to do, you got up, cleaned yourself up, packed a suitcase and headed to the airport. You assumed he was playing out Mamma Mia, so you knew it’d be summer there, so you made sure to pack cool clothing, and put on a beautiful but cool ankle-length, blue, spaghetti-strap dress, with white strap sandals with cork bottoms.   
When you got to Greece, you hopped in a cab and drove to the dock but when you got there the boat was just leaving. You, alongside a man who seemed to also want to catch the ferry, rushed to the end of the dock towards the boat, calling out for them to turn around, but of course they didn’t, so you missed the boat.   
“Bugger” said the man next to you. You finally had time to notice the man and when you did you forced yourself to stay in character. He had green eyes and light brown hair, and was none other than your cousin, the famous, Dean Winchester. He was wearing a black suit and sunglasses, just like Harry was in the movie, looks Lucifer’s done his research. But who would he play in this strange little skit?   
“My sentiments exactly” you reply trying to stay in character and not laugh. Really? Dean was Harry Bright? Who’d be Harry’s partner, Cas? You bit your lip to hold back your laugh and walked over to look at the boat timetable.  
“I’m trying to get to Kalokairi. When’s the next ferry?” Dean (Harry) asked as he walked over with you and tried to read the sign that was written half in English and half in Greek.  
You looked at the timetable, looked out at the water, then stood up looking defeated “Thasthera” you replied.  
“What?” Harry asked as he stood up looking confused.  
“Monday.” You translated for him.  
“Bollocks!” He sighed.  
“Yeah, my sentiments exactly.” You repeated, exasperated. “Bride or groom?” you asked, looking at Harry quizzically, as he looked at his invitation upset.  
“Bride, although I’ve never actually met her.”  
You look at him confused about to ask another question when a voice came from above, “Ahoy there,” he called out to you.  
You looked up and stifled a laugh. Really? What was it with Lucifer and getting his little brother involved with these things? He was wearing an outfit identical to that of Bill Anderson’s in the movie. Lucifer really wanted accuracy didn’t he? “You guys need a ride to Kalokairi?” Gabriel (Bill) asked ripping you out of your thoughts.   
You nodded and boarded the ship, you talked with Dean and Gabriel for a bit as Gabriel sailed the ship to the island. Hopefully Lucifer was unaware of you three breaking character, unbeknownst to you though he was fully aware, and would punish you for it later.  
“So, how do you like your little role play so far?” Dean asked you.  
You took this as permission to break character, and so you did, “It’s perfect. You wouldn’t expect Lucifer to be this sweet, but I mean this is proof enough that he’s not as vicious as everyone makes him out to be. So, I’m guessing you’re meant to be Harry Bright, and Gabriel you’re meant to be Bill Anderson.” You queried.  
“Yeah, that’s correct sweetcheeks.” Gabriel answered.  
“If that’s the case does that make me Sam Carmichael?” You asked curious to know who you were supposed to be. You were pretty sure from the lines you had said and what had happened so far that you were, but you were confused as to why, shouldn’t you have been one of the female characters.  
As if hearing your thoughts, which he probably did knowing him, Gabriel answered your questions, “That’s a bit complicated, you kind of share the role with someone else, but they also have another role which you share with them. And you’re not completely a female character because we weren’t able to get you to Kalokairi without spoiling the surprise. But everything other than your roles and the lines will be 100% accurate.”  
“I’m guessing you’re not going to tell me who I share my role with or who my other character is, are you? And it wouldn’t have mattered where I woke up, I’ve seen the musical enough times to know what a wedding invitation and a ticket to Greece generally implies, so the surprise was spoilt as soon as I opened the envelope.”  
Gabriel seemed to be smirking at your comment so you knew something was up, “what are you smirking at?” You asked slightly annoyed at his suspicious behaviour.   
“You’ll see, just… ‘Remember, play along’.” He quoted.  
“Argh” you shouted in frustration, standing up and walking off the boat as it docked on the shore.  
You stormed off and up the stairs to the villa at the top of the hill on the island. When you finally finished climbing up the stairs you turned around and looked out at the gorgeous view. When you turned back around Lucifer was standing there, you smiled at him and he walked over to you. What he said next tore you to shreds “I’m engaged to someone else and I have to leave,” he said. You couldn’t believe what he was saying, surely this had to be part of the role play. “Luci?” you whispered tearing up. He didn’t say anything he just vanished, his reaction made you realise, this wasn’t an act. You felt numb, and your ears were burning, this couldn’t be real. Did Lucifer really just say that, your Luci? Confused, upset and broken-hearted you ran off to your room in tears. (Little did you know that all of that was an act to help you transition into your other character. He wasn’t engaged, he still loved you and always would, and your reaction cut him like a knife. But surely you knew it was all an act, that he was playing the part of Sam Carmichael, didn’t you? It took all of his will and strength to stay gone, and not rush back to you, hold you in his arms and reassure you that none of it was real and that nothing and no one could ever take him from you).  
So now, here you were on your own, on an island alone and miserable, and the worst thing is the people that you loved, the people you trusted were in on this too. How could you ever trust anyone ever again. At least you had a villa to run, he’d left you with that. So you decided that’s how you would spend your time until you died, ‘hard work and a crippling mortgage.’  
A couple of months later on your way to the wedding you had been invited to (you were the Maid Of Honour), you ran into the one and only Lucifer, the prick was standing there with a bouquet of roses and a solemn look on his face, you scoffed at him in disgust. Did he really think that a puppy dog look and some dumb roses would make you forgive him?  
“Y/N, I’m sorry. I didn’t mean it, I didn’t think you’d react quite like that. It was meant to be for your surprise.” He said woefully.  
You walked up to him and punched him (the punch not affecting him in the slightest as he was an angel and you were just a human) your eyes welling up with tears. “It was definitely a fucking surprise you prick. How did you think I was going to react when you told me that?”  
“I thought you…” you cut him off waving away his words.  
It was your turn to sing now, “I don’t wanna talk. About things we’ve gone through.” You sing shaking your head as you do, holding your hands on your heart. Just like when Lucifer sang Sweet Transvestite instrumental accompaniment appeared out of nowhere, but this time just a piano, playing in minor key, it was both sad and beautiful.  
“Though it’s hurting me. Now it’s history” you continued. “I’ve played all my cards,” you sing raising your arms. “And that’s what you’ve done, too.” You hold your hand out to him in an almost open-handed point before pulling it back. “Nothing more to say, no more ace to play” you chuckle sadly and he sighs, wiping his hand down the right side of his face.  
“The winner takes it all” you sing turning away. “The loser standing small” you shrug, “beside the victory,” you sing turning back to him. “That’s her destiny” you shake your head as you sing.   
You take a step back and slowly wrap your arms around yourself as you sing the next line “I was in your arms,” you throw your arm up as if brushing the pain off, “thinking I belonged there. I figured it made sense, building me a fence” you sing looking up at him.   
You chuckled again “building me a home, thinking I’d be strong there.” You stroke his arm gently, “but I was a fool, playing by the rules.”  
“The gods may throw the dice,” you throw your arms out as if throwing a dice, “their minds as cold as ice” you touch your forehead then strike your arm out in a slicing motion, “and someone way down here” you point down “loses someone dear,” you wave your arm out.  
“The winner takes it all” as you sing Lucifer runs his hand through his hair, “the loser has to fall” he rubs the back of his neck, “it’s simple and it’s plain” you sing walking around him “why should I complain?” He brings his hand down as you bring both of yours up.  
“Tell me does she kiss” you put your hands over your mouth and bring them out like your blowing a kiss, “like I used to kiss you? Does it feel the same, when she calls your name?” You shrug slightly, “somewhere deep inside, you must know I miss you. But what can I say” He rubs his forehead, a look of sorrow and frustration crossing his face. You laugh and hold your hands against your cheek, your hands clasped together as in prayer. “rules must be obeyed.”  
With each verse your face gets redder and redder as you try to hold back your tears and sing, “the judges will decide” you sing holding your arms up as you look up to the heavens, “the likes of me abide” you hold your hands together under your chin as if in prayer. “Spectators of the show” you wave your left arm out “always staying low” you wave your right arm out as you turn and push your arms down.   
“The game is on again,” you start to sway from side to side, Lucifer bows his head and turns away, he turns back as you sing the next line, “A lover or a friend. A big thing or a small” you wave your arm around at him. “The winner takes it all” you raise your arms up, then around and out, then bring them back to you, forming a bit of a circle with your arms.  
He rubs his face as you bring your arms back around to hold yourself, “I don’t wanna talk,” you sing waving your arms back and forth as if to say you’ll have none of it. “Cause it makes me feel sad” you step forward, “and I understand” you take another step forward. “You’ve come to shake my hand” you stick your hand out for him to shake and he looks down, you pull it back and continue singing. “I apologise” you hold your hand to your chest and he rubs his forehead again, “if it makes you feel bad” you lean forward, “seeing me so tense,” you rock back and forth on your feet “no self-confidence, but you see” you wave your arms out.  
You bring them back to you before pointing back to him “the winner takes it all” you sing as you raise your arms up still pointing at him. “The winner takes it all” you grab at the air and clench your hand waving it near your chest. “The game is on again,” you belt turning as you do “a lover or a friend” you turn back. “A big thing or a small” you raise your arms above your head and bring them down and hold them out as you spin around “the winner takes it all!” you run off as you sing this holding the last note as you run away from him to the church. As you run, Lucifer turns and watches you for a second before running after you. You run up to the stairs to the church the piano still playing, when you get to the top of the stairs you pant for breath and Lucifer who’s standing on a cliff below you, waves crashing against the rock, calls out to you “Y/N!” You look back at him, face stained with tears, as you lean against a wall, and sing the last line. “The winner takes it all.”

**Notes for the Chapter:**

> Sorry guys, but hopefully all will end well...

**Author's Note:**

> Thanks for reading, hope you liked it. If you have any requests or ideas for chapters for this or anything else please feel free to leave a comment. Oh, and I got this idea from a youtube video I watched of Mark Pellegrino at a convention. https://www.youtube.com/watch?v=sH026hjRPVA


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